


Crossdressing Date

by Damien_Kova



Category: RWBY
Genre: Crossdressing, F/M, Public Sex
Language: English
Status: Completed
Published: 2017-12-06
Updated: 2017-12-06
Packaged: 2019-02-11 10:53:43
Rating: Explicit
Warnings: Creator Chose Not To Use Archive Warnings
Chapters: 1
Words: 2,744
Publisher: archiveofourown.org
Story URL: https://archiveofourown.org/works/12933729
Author URL: https://archiveofourown.org/users/Damien_Kova/pseuds/Damien_Kova





	Crossdressing Date

Jaune stood in place on an almost unknown street at the edge of Vale, waiting on his redheaded lover to arrive. The boy was wearing the dress he showed up to prom in, keeping a smile as he remembered just how odd it was to be wearing makeup like he was. Luckily, after about five minutes or so of standing around, he noticed his redheaded teammate approach in a tuxedo, a smile on her gorgeous face as well. “Another night all alone, Achilles? Or do you plan to take me somewhere as thanks for what I did as prom?~” Of course, the moment Pyrrha stepped close enough, their lips met in a loving and affectionate kiss.

 

“I thought I’d take you dancing tonight, Joan. It’s been so long since we were able to, and I just…. I think the time is right.~” A soft giggle left the redhead as she held her hand out for her date, just now noticing the makeup that her lover was wearing. “Oh wow. Good job on the makeup! I must say, you’re getting better!~” Even as Pyrrha continued to hold her hand out and wait for Jaune to take it, she couldn’t help but smile and think of how long it took to get right. “Of course, we’ll probably stop by a movie and dinner first to make sure the night lasts.”

 

“W-Well, when you grow up with seven sisters, you sort of learn. Especially when they’re sick and make you put it on them for some reason.” The blonde boy finally took the girl’s hand and forced a smile, actually recalling to how he sat in Glynda’s office for the blonde teacher to put the makeup on him.

 

\-----------------------------------------------------------------------------------------------------------------------------

 

“You know, Jaune, if you just took the time to ask Pyrrha, I doubt she’d mind teaching you!~” The older woman smiled and placed a very gentle kiss onto her student’s forehead, applying lipstick to his lips and stealing a quick kiss to make sure it’d stay in place when he and Pyrrha got heated. “Nothing more than a peck.” Glynda couldn’t stop herself from giggling as she watched a blush rise to Jaune’s cheeks.

 

“Well, I mean… with seven sisters, I should be able to do at least something like this, right?” The boy’s blush only grew worse as he heard his teacher start outright laughing at him. “Oh, come on! Can’t we just hurry up?! She’s gonna be waiting on me!”

 

“Does anyone else know you two do this?”

 

“No one. And she doesn’t even know that you’re in on it.” Jaune turned to the side and sighed softly, officially nervous about his date later tonight. “Why…?”

 

“Because she’ll have to sneak out. Meaning it’ll take awhile. So, hush and sit tight so I can finish.”

 

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Their night continued just how Pyrrha had planned things out for them. A nice movie that lasted a few hours with the two lovebirds sharing a few kisses at certain moments, and even some popcorn, before a romantic dinner at a nearby restaurant. Nothing fancy or over the top, or even flashy, but just a quiet meal in the middle of an unpopulated venue on the edge of Vale. Of course, kisses were shared, jokes were told, and laughs were had. But as Jaune stood up to leave, ready to pay for the check, he couldn’t help but smile as Pyrrha grabbed his hand and shook her head. “Sit down, Joan. I told you, already… Tonight’s on me.~”

 

The young redhead smiled as she used cash to pay for their bill, leaving a hefty tip for the waitress that came and helped and even complimented Jaune on his makeup. “Now…. Usually, we’d both want date night to end here…”

 

“Yeah… but, I don’t really want it to end. I’m having too much fun. Even if it’s just one more place, I’d love to go somewhere else before we go home.” Jaune smiled as he stood from the table, watching his date stand with him before they grabbed the other’s hand and headed towards the exit. “So…. One more stop, okay?”

 

“That’s what I had in mind. There’s supposed to be a formalish nightclub just a few blocks from here that hardly anyone goes to. I say we go there. We won’t see anyone we know either.” The redhead smiled and gently kissed the blonde’s cheek as they stepped outside. “And that’ll be the dancing I had promised you, too.~” Luckily, it only took a moment for Jaune to think on it before agreeing to go, watching him nod with an even larger smile than a moment ago. “Good!”

 

Jaune kept his smile as he walked with Pyrrha, even as the cool nighttime breeze would sometimes collect under the hem of his dress and lift it up to ever so slightly show off the red panties he was wearing. Even as it happened and he had to use his free hand to keep everything down to hide what he could, it still didn’t dampen his spirits about the date night the two were on. Everything was going perfectly for them and they had no interruptions or reasons to hide.

 

Of course, as they entered the nightclub and heard music blaring, even if it was almost as unpopulated as Pyrrha said, they both kept their smiles as they held the other’s hand. First stop for them both, however, was the bar to get a drink. “Just something non-alcoholic and fruity for my date.” Achilles put on her best voice as she spoke to the well built bartender. “And a glass of water for me.”

 

“Coming right up.”

 

“Really? Fruity and non-alcoholic?” Jaune asked, doing his best to sound feminine and play the part, earning a large grin from his redheaded companion. “Oh, don’t give me that look. You know damn well why I’m doing this.” Before their drinks could even be placed beside them, the two broke out into a near infectious laughter. Fortunately, it only affected the two of them before the blonde felt his well-dressed lover’s hands on his hips and felt her lips collide with his own in a heated kiss, but it was a heartwarming moment for him nonetheless. It didn’t help that he could feel Pyrrha’s lips curl into a smile as they stood there together.

 

However, after their kiss had ended, the two made their way to the dance floor just a few feet away. Neither one cared enough about their drinks to take them, figuring they’d be fine where they were since the nightclub wasn’t packed like most other ones. A slow song came on when they first got onto the dance floor, causing them to smile and wrap their arms around each other, both now used to the fact of having to play the other role when it came to nights like these, and neither one caring as they danced together. Unfortunately, as they danced together, Jaune couldn’t help but notice a man almost twice his age casually attempting to pull him to the side away from Pyrrha while a woman did the same to his redheaded date.   
  
“Sorry, we just couldn’t help ourselves when we saw how passionate you two were towards each other by the bar. We were wondering if you’d be able to share that passion with a couple of swingers tonight.” The woman spoke up from behind Pyrrha as the man who was trying to get Jaune stood beside her, all four of them now making eye-contact as everyone danced around them. “If that’s okay, of course. We wouldn’t bother trying to force you into something you didn’t want.”   
  
“Of course not, we just love seeing passionate people be willing to share that with someone else. It’s why we got into swinging in the first place.” The man smiled as he planted a kiss on the woman’s cheek. “Better to keep it anonymous as well so no one can get attached.”   
  
“Sorry, but…. I’m gonna have to say no.” Pyrrha said with a forced smile. “Not to be rude to you, you both are very attractive, but it’s just not what me and my partner, Joan, are into.” The redhead wrapped an arm around her blonde lover’s waist and kissed his cheek. “Sorry.”   
  
Jaune nodded and held Pyrrha close, clearing his throat to speak in a feminine voice to match his role yet again. “And, we don’t mean to be rude, but we did leave our drinks at the bar. We’re gonna get them. Don’t want anyone to take them, after all.~” The blonde smiled as he waved to the swinger couple, pulling Pyrrha long with him until they arrived at the bar and got their drinks, paying for them then and there. “Let’s find somewhere private. That way we can just enjoy ourselves and tonight without any more interruptions.”   
  
The redhead simply nodded and smiled genuinely, looking around the room before pulling her boyfriend to a booth just off the edge of the room that people would have to try and peek into if they wanted to see what was going on inside. Luckily, when the two arrived, it was empty. “So… What do you say we have some more…. Private fun, love?~” Pyrrha asked, licking her lips and starting to undress herself just enough to get her breasts out of her tuxedo.

 

Keeping his dress on, Jaune was more than eager to push Pyrrha back into her seat, plopping himself into her lap and starting to give her a slow lap dance. Every moment of his hips and every time the blonde would push himself back against the redhead’s body was just another motion that made the ‘man’ of the date smile. Even if it was amateurish and untalented, it was still more than enough to get them both going before Jaune felt a hand on the back of his head. “Hmm?” He asked, trying to sound innocent as he turned to his lover.

 

“Get under the table.” She said clearly, using her other hand to get her clothing down to her knees while she had the chance. Her plan was to stay as clothed as possible, but when the need arose and she felt her core ache, the redhead knew she needed him eating her out. And with a smile on her face, she gently pushed him down to do just that, biting her lip and spreading herself as much as she could to make sure he could fit under the table. After a moment or two of feeling his lips kiss her inner thighs, she finally felt that magical touch she craved, loving the way his tongue worked around her folds.

 

It wasn’t the first time Jaune had been in between his girlfriend's slender legs, even in public as well. That’s why the moment his tongue met her entrance, he was quick to swirl his tongue from the outside in, moving slowly at first and teasing her clit before speeding up as he neared the center. Of course, that burst of speed was more than enough to bring a moan from his emerald-eyed lover’s lips, and that was exactly what he was hoping for, relishing in the sounds and feeling of her legs attempting to wrap around his head, only to be denied because of their clothing.

 

Pyrrha was loving every second of this, the thrill of being caught by someone while being denied the perfect touch of being able to feel her thighs against her lover’s blonde hair, and even the way that Jaune knew she was trying and simply buried his face into her crotch even more. However, even with her hands tangled into his golden locks and his face buried between her thighs, the redhead knew he wasn’t going to push his tongue into her just yet, if at all. She knew he loved to tease like that, having grown to love it herself, but as she felt his teeth gently clench around her clit, the ‘man’ of the night wasn’t able to stop the blissful yelp that left her. Fortunately, the Mistral girl was able to clamp her hand over her mouth just in time to keep anyone from looking towards them. But that ache was still there and failing to go away as she pulled her lover as tight against her core as she could. “Please, Joan…. Fuck me against the table….”

 

\--Now that was an invitation that Jaune wouldn’t dare pass up, more than happy to grab hold of his redheaded lover’s hips before spinning her around and pushing her against the table. Without hesitation, the blonde boy flipped part of his dress over Pyrrha’s ass and slowly guided his cock into her dripping entrance, eliciting a sharp moan from the girl for just a moment before one of her hands reached back and held her ass just enough to spread it for him. With a smile, the ‘girl’ of the night leaned down against his girlfriend and reached a hand around her torso to grab hold of her breast, already starting to thrust at a pace he knew the champion loved. Rough, fast, and filling her up while hitting the perfect spots inside of her. “Oh fuck, I’ve missed this.~”

 

“You say -oh fuck me, right there!- like it’s been weeks since you’ve….. Fucked me…” Pyrrha commented, smiling as her free hand gripped the other side of the table to help stop her body from jiggling and shaking the only thing that was currently keeping her standing. Even as she closed her emerald eyes and let the pleasure wrack through her body, teasing her lover in the process, there was no denying the bliss that seemed to radiate through her from him fucking her so thoroughly, even if she wanted to just to push Jaune that much harder to get her off. However, with the feeling of his hand firmly wrapped around her breast and tweaking her nipple just a little bit, there was no quieting herself down either, moans leaving the secluded booth they were in and probably alerting a few people to what they were doing. Not that she was complaining as she felt herself nearing the edge of her orgasm.

 

Luckily, as Jaune looked around the booth to make sure that no one was coming due to the loud and pleasured noises that were leaving his lover’s mouth, making the blonde smile and bite into Pyrrha’s neck. Whether he liked it or not, his orgasm was approaching hotly and much faster than he would’ve wanted, but as the redhead’s cunt started spasming and quivering around his thick shaft, part of him didn’t mind. It was almost like the Mistral girl had wanted him to cum already, knowing how much he would love this moment and have the urge to cum inside of her.

 

“Cum inside me, Jaune! I’m getting so close and want it! I need your cum!~” Pyrrha threw her head against the table as she screamed out into the booth, her orgasm hitting her incredibly fast and hard as she felt her boyfriend’s cock pound against her cervix with each thrust he made. Much to her surprise, as the redhead bit her lip and came hard around her lover’s cock, she felt a torrent of cum flood into her womb and filling her entirely. “Oh fuck!~”   
  
Even as Jaune came inside of his well-dressed lover, he didn’t stop squeezing her breast and rolling his hips, letting her feel what it was like to have a cock moving inside of her as she was stuffed full of cum. After a moment or two, the blonde boy slowly pulled his length out of his lover, groaning as he fell back into the booth and let some of his cum stain the bottom of his dress. “Pyrrha… That…. That was amazing…”

 

“Damn right it was… What… What do you say we stay here… And rest?” The happily lustful smile on her lips was all she knew it would take to convince Jaune to stay with her as she planned to fall asleep in her lap. “I love you, Jaune…” Keeping her smile, Pyrrha fell back into her boyfriend’s lap and wrapped her arms around his neck, turning her head to plant a loving kiss on his cheek and giggling as she felt his hand remain on her breast while the other found its way to her hip.

 

“I love you too, Pyrrha. Just an hour and we’ll leave.~”


End file.
